Three new resin glycosides and a new tetrahydropyran derivative from the seeds of Quamoclit pennata

Chem Pharm Bull (Tokyo). 2012;60(8):1083-7. doi: 10.1248/cpb.c12-00334.

Abstract

Three new resin glycosides, quamoclins V (1), VI (2), and VII (3) and a new tetrahydropyran derivative, quamopyran (4), were isolated from the seeds of Quamoclit pennata BOJER (Convolvulaceae). The chemical structures of these compounds were determined primarily on the basis of spectroscopic data. The carboxyl group of the aglycone, 11S-convolvulinolic acid, of 1 and 2 was linked intermoleculary with a hydroxy group of the sugar moiety to form a macrocyclic ester structure, as in already known jalapins, and 3 was an acylated glycosidic acid methyl ester. All of the sugar moieties of 1-3 were acylated by one 2S-methylbutyric acid. Compound 4 was a diketone having a tetrahydropyran ring.

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Convolvulaceae / embryology*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Pyrans / chemistry
  • Pyrans / isolation & purification*
  • Seeds / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Glycosides
  • Pyrans